Honestly, I get the impression that he's easily outflanked by smart people. And that something about his personality drives people to take advantage of him. That impression comes from his apparent business incompetence. He is capable of screwing up "sure things" such as casinos and hotels. Best I can tell, he ends up getting a raw deal, then proceeds to make the shit roll down hill by screwing over people down stream of him (i.e., not paying contractors).

He's clearly a capable actor. He pretends, rather convincingly, to be this amazing, confident, shrewd businessman. And I think a lot of people idolize him because he embodies what they think of when they think of a smart, successful business person. But I think real smart, successful business people spend two minutes with him, and paint him as a rube.